Multifunctional Logic in a Photosensitizer with Triple‐Mode Fluorescent and Photodynamic Activity

Abstract

Herein we describe a photosensitizer (PS) with the capacity to perform multiple logic operations based on a pyrene-containing phthalocyanine (Pc) derivative. The system presents three output signals (fluorescence at 377 and 683 nm, and singlet oxygen ((1)O2) production), which are dependent on three inputs: two chemical (concentration of dithiothreitol (DTT) and acidic pH) and one physical (visible light above 530 nm for (1)O2 sensitization). The multi-input/multioutput nature of this PS leads to single-, double-, and triple-mode activation pathways of its fluorescent and photodynamic functions, through the interplay of various interrelated AND, ID, and INHIBIT gates. Dual fluorescence emissions are potentially useful for orthogonal optical imaging protocols while (1)O2 is the main reactive species in photodynamic therapy (PDT). We thus expect that this kind of PS logic system will be of great interest for multimodal cellular imaging and therapeutic applications.

New application of phthalocyanine molecules: from photodynamic therapy to photothermal therapy by means of structural regulation rather than formation of aggregates

“…, amino group) on the Pc structure can efficiently quench Pc's fluorescence emission and reactive oxygen species (ROS) generation. 10 Thus, we first compared the photothermal effect of two Pc compounds peripherally substituted with amino groups (PcA1 and PcA2). Their chemical structures are displayed in Fig.…”

Activatable Photosensitizers: Agents for Selective Photodynamic Therapy

“…[81] In a more recent report, Torres et al also described a pH and thiol dual-responsive aPS that contains a pyrene-modified SiPc group, which should attract great interest as a multifunctional theranostic agent. [82] Recently, Liu et al described a series of special fluorophores that possess aggregation-induced emission (AIE) characteristics that can be used advantageously in the design of new aPSs. [83][84][85] One system is a dual-selective enzyme-responsive bioprobe containing a PS for cancer-specific imaging and activatable PDT.…”

Alkane Chain‐extended Pterin Through a Pendent Carboxylic Acid Acts as Triple Functioning Fluorophore, 1O2 Sensitizer and Membrane Binder

“…Over the past 6–8 years, “smart” compounds that possess dual fluorescence sensing and singlet oxygen sensitizing properties have become a hot topic , with success reported in dual function image‐guided and photodynamic therapy applications (PDT) . Indeed, our previous O ‐ and N ‐decyl‐pterins possessed good singlet oxygen quantum yields (Φ ∆ ), but had poor fluorescence quantum yields (Φ F ) some 4–30 fold less compared to native pterin, thereby fulfilling only two of three facets, even though a minor fluorescence increase was observed when intercalated in the membrane .…”